Prom Night
by Rant Girl
Summary: Written for the prompt: Either hooker!Jess or Hooker!Dean, Stanford wasn't the first time they met.  - Jessica's big sister hires her an escort for her senior prom.


"Beth you are so dead."

"Jess-"

"I can't believe-...if mom or dad ever find out-"

"Which they won't-"

"They won't get a chance to kill you, because I'll do it first," said with a conviction that is rarely achieved outside teenage hormone fuelled melodrama...

"You're completely over-reacting."

"When you said you'd get me a date I thought you meant one of your college buddies. You hired me an _hooker_, for my senior prom!" ...though in this case it might have its legitimacy.

"Escort," says Beth quietly.

"What?" Jessica dares her to challenge her on this.

"He's not a hooker, he's an escort, and he is off the charts hot-"

"Oh because that makes it so much better."

"You wait 'til you've seen him."

"I don't _want_to see him," she says almost pleadingly, not getting why her sister doesn't just understand how this is so not okay.

"You know what. I paid a fairly substantial amount," _of the money their parents had given her_Jess just rolls her eyes, "...so quit complaining. You are going to that prom. You're not going to give that asshole, who dumped you two days before it I might add, the satisfaction of you not being there. And don't give me that look, you cannot go alone. That sends the wrong message."

"Oh but paying someone to take me sends the right one?"

"Jess, I'm telling you, this guy could make water jealous. Besides you can take full advantage of all of his _services_. You're old enough."

Jessica just scoffs, at a complete and utter loss of words. Shaking her head she turns away from her sister. She can't even look at her right now she's so pissed.

"Now get back upstairs and finish getting ready, unless you want to go in your underwear."

Jessica sighs, hanging her head she clenches her teeth to stop herself from screaming before thundering upstairs and slamming her door so hard that it just flies back open.

* * *

><p>Dean shifts in his seat, tugging at the collar of the shirt he's wearing. He friggin' hates these stupid monkey suits. But the email had said <em>'formal wear essential'<em>, and apparently there had been a special request for him. Dean smirked rather smugly at that. That part he likes. Though of course it isn't his first. He knows how hot he is. But he's not really looking forward to this, the suit and tie are one thing, but he was also told to get a corsage, and that means one of two things; it was some cookie old broad (the arrangements were made kind of last minute so he didn't have the time to ask for the full details) or a high school dance. He doesn't do dancing. But he needs the money.

He checks the address again before turning into the street of a rather swanky neighbourhood. They usually were. No one else could afford it. He double checks the house number after he parks, and takes a deep breath before grabbing the corsage and getting out of the car. He _caresses_the hood, taking comfort from the solidity of it. "Alright baby, here we go," he mutters under his breath, walking up to the door to ring the doorbell, but the door opens before he has the chance.

"Wow. Even better than your picture," the girl who answered the door, in her sweats, eyes him up and down, "Perfect, just what she needs," and she grabs him by the arm, "Come on in," and she closes the door behind him, "She's upstairs," she tells him before disappearing into some other room, leaving him in the foyer.

Dean just blinks, not really sure what he's supposed to do, "Go on up," comes the instruction from what he assumes to be the living room, and he finds his legs moving without even deciding to do so. He looks back down over the banister wondering if the girl will re-appear, but every thought goes out of his head when he gets to the bedroom door. His _date_is standing in front of a dresser, her back to him. His eyes scan down her body, lingering on the lace panties that just barely cover her ass, and down, all the way down to her shoes. Girl's all legs. And toned, he definitely lucked out tonight...he jumps a little when she lets out a yelp.

"God, don't you knock!"

Jessica quickly snatches up her dress to hold up in front of her, before turning to face him, though resolutely keeping her eyes on the floor. _Jesus_, he scared the crap out of her. What the hell was her sister thinking sending him up here. He saw her in her underwear! She was going to tell him to get the hell out but then she looks up into his face and she freezes. She didn't know it was humanly possible for one man to look that hot. She shuts her mouth the second she realises it's open and then clears her throat, shaking her head a little to try and get her brain to function, "Uh...would you mind...turning around?"

"What-...uh yeah," he says as if snapping out of his own trance. Her eyes track the movement of his throat as he turns his head before turning his body away completely. What she would give to lick it...she did not just think that, "Yeah, uh, sorry."

She bites her lip, "It's fine," she says before turning back to her mirror giving her make-up another once over before slipping into her dress. She glances at him over her shoulder, wishing she could get a better look at his ass, "Hey, would you mind..." and she waits 'til he turns back around, moving her hand behind her back to indicate the zip.

"Uh, sure," she hears him gulp and she smiles to herself, her back arching just ever so slightly at the feel of his fingers, feeling the tension drain from her shoulders.

* * *

><p>Dean pulls the zipper up delicately not wanting to catch her skin, or the material, it would be just his luck that he'd ruin her dress or something, and something tells him this girl has a great right hook. A smile forming on his lips as she shudders slightly, "You are legal right?"<p>

He watches her in the mirror as she tilts her head up to look at him in the reflection, arching her brow, "Why? There an age limit on zippers I don't know about?" she shakes her head, letting her hair fall about her shoulders before she pulls it back, twisting it round to hold it up and away from her neck, "I am eighteen, yes. What about you?"

"Twenty-two," he tugs the zipper to the top and then smoothes his hand down her back, taking her wrist in his other hand, to pull her hand away from her hair, "There."

"Thanks," she says softly, turning back to him, lips slightly parted. He brushes her hair back behind her ear. _God she's beautiful._And with her heels on she's a good few inches taller than Dean, but he definitely doesn't mind. He picks up the corsage, removing it from its box and slides it onto her wrist. He doesn't take his eyes off her. He holds her gaze for at least thirty seconds before she looks away.

"Ready?" he asks with that mega-watt smile, to which she only nods in reply. The girl who he is assuming is her sister nearly blinds them as they reach the bottom of the stairs as she takes their picture. Dean takes the initiative to actually stop to pose for one, figuring that if she wanted to keep it, it should look at least half decent. Glad when they get outside to the open air.

"That's your car?" and the way she says it, he knows she's impressed.

"Yep, that's my baby."

"And she doesn't mind your _extra-curricular_activities? Not many girls would agree to an open relationship."

"Cute."

"I like to think so."

* * *

><p>When they get inside the car, that's when Jessica starts to feel nervous. And she hates her sister just that little bit more. This is so crazy. Why did she even leave the house? She jumps a little, her breath sharp as he shakes her shoulder, apparently he'd asked her something, "What?"<p>

"Hey, are you alright?"

"Yeah, sure, I'm fine," which she says, rubbing the back of her neck, the look on his face, when she gets the courage to actually look at him, telling her he doesn't believe her in the slightest.

"Look nothing's going to happen here that you don't want, but I'm going to need you to relax. _You_need you to relax. Prom's supposed to be fun right?" his voice is soft, and she feels oddly better when he takes her hand, the brush of his thumb tickles a little and she gives him the smallest of smiles.

"Yeah, I guess," she says, looking down at her lap as she smoothes out her dress.

"You don't want to go?"

"Yes. No. I mean," she sighs, "I wanted to go yeah...I just...I don't want to see..."

"Don't want to see what?" he prods gently.

"Him," her voice engulfed by the weight of it, she's still kind of pissed. This whole thing is humiliating, but knowing she's probably not going to get out of this conversation without further elaboration she continues, "This stupid jerk that broke up with me two days ago..."

* * *

><p>Dean mentally kicks himself for prying, why didn't he just leave it? "Because you didn't want to have sex?" it's a guess.<p>

"No," and wrong apparently, "We had sex, and apparently if I'd waited 'til prom I still would of had a date, what was it he said, 'I don't do double dipping'," she just rolls her eyes, but Dean, he feels kind of annoyed, this guy, whoever the hell he is, is clearly a grade A douchebag.

"Want me to beat him up?"

"What? No. I mean if that asshole had, had the balls to confront me face to face instead of over the phone, I would have wailed on him myself."

That makes him laugh and he shakes his head, "Now that I would pay to see. So do I get to know your name?"

"Oh god, that's embarrassing," and she actually blushes, "am I like the single rudest person on the planet?" not in his book, "It's Jessica."

"Jessica?" he tilts his head in consideration, yeah she was definitely a Jessica, "I like it. I'm Dean."

"Dean. I guess can work with that."

"Brat," he says fondly.

"No calling me a brat," she says with a playful swat.

"Yes ma'am," earning him another swat as he tips his imaginary hat.

"No calling me that either."

* * *

><p>They had only stayed at the prom for about an hour, after making their <em>grand<em>entrance, and watching her ex storm off, leaving his date trailing after him, the novelty of revenge sort of wore off. As did her tolerance for the rest of the students in her class. All that was left to do was to roll up a bunch of food in some napkins and then they were gone. And now she was sitting in the car outside of a 7/11. Dean was buying what she suspected was beer. He'd promised to take her somewhere special.

It came as a surprise to her that she didn't even really mind if _somewhere special_translated to a motel, but as it turns out...

"You brought me to a field?" her brow arched, in a _are you for real_type of way.

"Don't say it like that. It's supposed to be romantic."

_Romantic_? Were escorts supposed to be romantic...she guesses they are, or well why else would they have them right? But still, "A field?"

"Come here," and he grabs her hand, pulling her back over to the car and to him, "Okay, I want you to close your eyes, come on."

"Okay," and she does though she feels a little silly, a feeling that only intensifies as he pulls her in against his chest. Though that could really just be the bottom of her stomach falling out. Her breathing slows, "Look up," he whispers, and she opens her eyes, the stars coming into sharper focus, and she can't help but gasp, "It's beautiful."

"Not the only thing that is."

"Was that a line?" she asks, amused.

"Cut me some slack here."

"Rough night?" tilting her head back onto his shoulder to look at him, she pulls his arms around her waist.

"Not exactly."

"Then what is it exactly?"

"You're really hot."

"I'm sorry it's such a hardship."

"Oh there's something hard, but it's not exactly a ship."

"You gonna plough me?" she says in a mock seductive(read: porno) tone, grinding her ass back against his erection.

* * *

><p>Dean's eyes flutter shut, and he pulls her closer, if that's possible, before her words fully register, and it was his turn to arch his brow, though he couldn't keep the dirty grin from his lips, "Seriously?"<p>

"You're the one who brought me to a field."

Dean shrugs, "Touché," walking his fingers along her collar bone, he has the perfect view of her cleavage from this angle, "Do you want me to?"

"You have to seduce me first."

"It's your money."

"It's my sister's money."

"Well then I'm sure she'd want you to get her money's worth."

Jessica laughs at that, "Smooth."

And he chuckles right along with her, he likes her, and for some reason he just can't hold up any sort of pretence with her, "How about a beer?"

"I would love a beer," she says it slowly, her voice dripping with honey, and when she breaks from his embrace, turning to face him, he can't help but just pull her back in, and their lips meet. Dean sucks on her top lip gently, and then the bottom one, tugging with his teeth. Their tongues melt together as they touch, the taste of whiskey mixing with watermelon. Her fingers thread through his hair, make his scalp tingle, his own making quick work of the zip of her dress, the material almost flutters down to pool at her feet.

She shudders as the cool night air hits her skin, quivering anew when Dean slides his hands down her back, cupping the curve of her ass. He picks her up sitting her up on the hood of the car, it still has a residual heat from the engine, mouthing over the material of her bra he teases her nipple with his tongue eliciting a whimper from her lips followed by a chocked off giggle as his fingers ghost over the front of her panties. He places a kiss at the hollow of her throat, very slowly increasing the pressure of his fingers and she rolls her shoulder against her cheek, throwing her hands back for support.

"Dean, please..." he lets his fingers slip beneath the lace, his knuckle dipping into the wet slit of her pussy, teasing her clit on every stroke, his lips mapping her jaw line. Jessica grabs hold of his tie, tugging him into a kiss, loosening it off enough to let it slip to the ground. Her hands fumble at the buttons of his shirt. She needs to feel flesh.

Dean loves working a girl into a frenzy, and he chuckles low and dirty into the next breathless kiss as she manages to pop the buttons of his shirt in one motion. Her hands more certain this time. She drags her nails down his chest, her bottom lip trembling as he pushes two fingers up inside her. Dean captures that lip between his teeth, pressing the bulge of his cock against the edge of the Impala, the dress pants he's wearing not offering sufficient friction.

Just as quickly as she wrapped herself around him, she pulls her arms away, leaning back on her hands, and then shifting herself forward, unable to keep still. She tugs him in by his belt, a cry tearing from her throat when he changes the angle of his fingers, "Please, I ne-need...please," and she forces her eyes open, her pupils completely blown. Her body quaking under the effort of it. Dean manages to unfasten his pants one handed, a slur of vowel sounds tripping from Jessica's lips as he removes his fingers, lining his dick up with her entrance, her back arching as he pushes in.

"Ngugh," her breath harsh as he pulls her down, her ass falling off the side of the car, arms flat out against the hood, her legs tighten round his waist, moving with him, 'guiding' him on every thrust, their rhythm getting more and more erratic.

"God, Dean," he could feel her tensing, pulsing around him, her nails digging into his shoulders as the sheer force of her orgasm pushes her into a sitting position. Her body quakes like every molecule of her being were on fire, and she collapses backwards when it's all over. Though she doesn't stop trembling, the aftershocks still taking hold in her veins, as Dean arrives to his own completion with a roar, laughter stealing what was left of his breath as he crumples on top of Jessica.

"Feel better?" his voice gruff.

"Best. Prom. Ever," she breathes, her voice equally wrecked.

Dean smirks into her skin, "I'll drink to that."


End file.
